22398-14-7

Basic information

• Product Name: DIMETHYL METHOXYMETHYLENEMALONATE
• Synonyms: METHOXYMETHYLENEMALONIC ACID DIMETHYL ESTER;DIMETHYL METHOXYMETHYLENEMALONATE;MMMM;Dimethyl methoxymethylenemalonate, 98+%;Dimethylmethoxymethylenmalonat;Propanedioic acid, (methoxymethylene)-, dimethyl ester;2-methoxy-5,5-dimethyl-1,3-dioxane-4,6-dione;DiMethyl 2-(MethoxyMethylene)Malonate
• CAS NO: 22398-14-7
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.15
• EINECS: 244-957-4
• Product Categories: fine chemicals
• Mol File: 22398-14-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 40-44 °C
• Boiling Point: 98 °C (0.5 mmHg)
• Flash Point: 158 °C
• Appearance: White/Crystalline Solid
• Density: 1.2311 (rough estimate)
• Vapor Pressure: 0.292mmHg at 25°C
• Refractive Index: 1.4390 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DIMETHYL METHOXYMETHYLENEMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL METHOXYMETHYLENEMALONATE(22398-14-7)
• EPA Substance Registry System: DIMETHYL METHOXYMETHYLENEMALONATE(22398-14-7)

Safety Data

• Hazard Codes: Xn
• Statements: 43-36/38-22
• Safety Statements: 37/39-26-24
• Hazardous Substances Data: 22398-14-7(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline solid

Uses

Dimethyl 2-(Methoxymethylene)malonate is a useful synthetic intermediate. It is used in preparation of (phenoxyethoxy)quinolones with antimalarial activities. It is also a reagent used in the synthesis of bicyclic pyridones prepn. as oral selective CB2 agonists with anti-pruritic activity.

InChI:InChI=1/C7H10O5/c1-10-4-5(6(8)11-2)7(9)12-3/h4H,1-3H3

Upstream product

• 108-59-8 malonic acid dimethyl ester 
• 149-73-5 trimethyl orthoformate 
• 104286-69-3 (R)-4-Methoxy-4,5-dihydro-pyrazole-3,3-dicarboxylic acid dimethyl ester 
• 99366-49-1 (4R,5S)-5-Dimethoxymethyl-4-methoxy-4,5-dihydro-pyrazole-3,3-dicarboxylic acid dimethyl ester 
• 27931-91-5 hydroxymethylenemalonic acid dimethyl ester 

Downstream Products

• 72179-89-6 2-benzyl-1,1,3-trioxo-1,2,3,6-tetrahydro-1λ⁶-[1,2,6]thiadiazine-4-carboxylic acid methyl ester 
• 18856-69-4 dimethyl (dimethylamino)methylidenemalonate 
• 125031-58-5 Methyl 1-(t-Butyl)-1,2-dihydro-5-methyl-2-oxo-3-pyridinecarboxylate 
• 125031-50-7 Methyl 1,2-Dihydro-6-(p-methoxyphenyl)-2-oxo-3-pyridinecarboxylate 
• 91586-27-5 6-(4-Methoxy-benzoyl)-2-oxo-5,6,7,8-tetrahydro-2H-pyrano[3,2-c]pyridine-3-carboxylic acid methyl ester 
• 125031-47-2 Methyl 1,2-Dihydro-2-oxo-6-phenyl-3-pyridinecarboxylate 
• 149742-99-4 methyl 1-(2,2-dimethoxyethyl)-2-(4-fluorophenyl)pyrimidin-6(1H)-one-5-carboxylate 
• 27931-91-5 hydroxymethylenemalonic acid dimethyl ester 
• 61559-23-7 dimethyl methoxymethylmalonate 
• 85531-80-2 methyl 2-oxo-2,5,6,7,8-pentahydro-2H-benzo[b]pyran-3-ylcarboxylate 
• 750647-64-4 2-[(2,3-diphenylquinoxalin-5-ylamino)methylene]malonic acid dimethyl ester 
• 462118-57-6 dimethyl benzoylaminomethylenemalonate 
• 862785-22-6 2-methoxy-4-[1-(3,4,5-trimethoxyphenyl)-meth-(Z)-ylidene]-dihydrofuran-3,3-dicarboxylic acid dimethyl ester 
• 862785-15-7 2-methoxy-4-[1-(4-methoxyphenyl)-meth-(Z)-ylidene]-dihydrofuran-3,3-dicarboxylic acid dimethyl ester 

Relevant articles and documents

NMR spectroscopic data of some 1-alkoxy-2,2-di(carbonyl, carboxyl, cyano)-substituted ethylenes

The 1H-13C NMR shifts as well as 1H and 13C coupling constants of 14 alkoxymethylene malonic acid and acetoacetic acid derivatives and two alkoxymethylene acetylacetones are reported. The 17O NMR spectra have been recorded for six of them. The long-range coupling 3J(H-C=C-CR) has been used for determining the stereochemistry of the double bond. Copyright

Method for the preparation of alkoxymethylene compounds of acetic esters and substituted acetic esters

Disclosed is a method for preparation of alkoxymethylene compounds, especially methoxymethylene compounds, from substituted or unsubstituted acetic acid alkyl esters, especially methyl esters, from the corresponding hydroxymethylene compounds or their alkali salts, by reaction with excess alkanol, especially methanol, in the presence of HCl and a water-binding agent. Preferred are water-binding agents which form stable reaction products with water.

SYNTHESE ET REACTIVITE D'OXYCYCLOPROPANES ELECTROPHILES

"Electrophilic oxycyclopropanes" 4 to 6 have been prepared starting from olefins 7.Ring opening of these cyclopropanes occurs under very smooth conditions (DMSO, room temperature).A push-pull type system is then also a powerful driving force with regard to the C-C bond cleavage in cyclopropanes.